Over the past few decades, ylide chemistry has been significantly extended to an area beyond olefination and small ring formation, among which ylide [4 + 1] annulation has been extensively explored, and five-membered ring structures, such as dihydrofurans, isoxazolines, pyrrolines, indoles, dihydropyrazoles and cyclopentenones, can be readily constructed through this type of transformation. An overview of the recent advances in this field is presented herein. Ylide [4 + 1] annulations are reviewed by highlighting their product diversity, selectivity and applicability, and the mechanistic rationale is presented when possible.